Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl 3-amino-6-bromopicolinate | HCID 25137688 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86697770 | HCID 86697770 | 70% |
Reaction Steps
A stirred suspension of ethyl 3-amino-6-bromopyridine-2-carboxylate (5 g, 20.3 mmol) in ethanol (40 mL) in a steel bomb was treated with a 2M solution of ethylamine in THF (220 mL, 440 mmol) and heated to 120° C. for 2 days. The reaction mixture was cooled to RT, the solvents were evaporated under reduced pressure and the residue was purified by column chromatography (SiO2, 0.5% methanol in dichloromethane) to give 3.5 g (70%) of the required material as white solid 1H NMR (400 MHz, CDCl3) δ 7.77 (brs, 1H), 7.21 (d, J=8.8 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 5.99 (brs, 2H), 3.4 (q, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133224B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-6e67024dfa084405b087928f514fc002 |
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| Source note | uspto-grants-2015_09 |
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